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US 10,651,403 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsMingjuan Su, Walter Yeager, Alan DeAngelis, Bin Ma, Lichang Zeng, Chuanjun Xia
Life of this patent
Estimating the term…
Abstract
The present invention includes a new series of benzofused heterocyclic ligands for metal complexes. These complexes show promising photophysical performance when incorporated into OLEDs.
Claims16
A compound comprising a first ligand LA having Formula I:
- wherein ring B is a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein RB represents mono to the possible maximum number of substitution, or no substitution;
- wherein Z1 and Z2 are each independently selected from the group consisting of carbon or nitrogen;
- wherein A1, A2, A3, and A4 are each independently CR or N;
- wherein ring C is a 5 or 6-membered aromatic ring;
- n is 0 or 1;
- wherein when n is 0, A8 is not present, and A5, A6, and A7 are each independently selected from the group consisting of CR, NR′, O, S, and Se;
- wherein when n is 1, A1, A2, A3, A4, A5, A6, A7, and A8 are each independently CR, and the Rs of two adjacent A5, A6, A7, and A8 are joined together to form a six-membered ring fused to ring C;
- wherein each R and R′ in CR or NR′ can be the same or different;
- wherein X is O, S, or Se;
- wherein the ligand LA is coordinated to an Ir atom;
- wherein the Ir atom is bonded to ring A through an Ir—C bond;
- wherein the Ir atom is also coordinated to at least one of:
- (1) a ligand LB and the compound has a structure Ir(LA)(LB)2, wherein LB has a structure
- wherein X1, X2, X3, X4, X5, X6, X7, and X8 are C, wherein Ra and Rb are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, or
- (2) a ligand LC and the compound has a formula of Ir(LA)2(LC), wherein LC has a structure
- wherein Ra, Rb, and Rc are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, and combinations thereof;
- wherein, when the Ir atom is coordinated to LB, Ring B is pyridine, Z1 is nitrogen, Z2 is carbon, and n=1;
- wherein each R, R′ and RB is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein any adjacent substituents are optionally joined or fused into a ring;
- wherein the ligand LA is optionally linked with ligand LB or ligand LC to comprise a tetradentate or hexadentate ligand.
18 more elements
An organic light-emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an organic layer, disposed between the anode and the cathode, comprising a compound comprising a first ligand LA having Formula I:
- wherein ring B is a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein RB represents mono to the possible maximum number of substitution, or no substitution;
- wherein Z1 and Z2 are each independently selected from the group consisting of carbon or nitrogen;
- wherein A1, A2, A3, and A4 are each independently CR or N;
- wherein ring C is a 5 or 6-membered aromatic ring;
- n is 0 or 1;
- wherein when n is 0, A8 is not present, and A5, A6, and A7 are each independently selected from the group consisting of CR, NR′, O, S, and Se;
- wherein when n is 1, A1, A2, A3, A4, A5, A6, A7, and A8 are each independently CR, and the Rs of two adjacent A5, A6, A7, and A8 are joined together to form a six-membered ring fused to ring A or ring C;
- wherein each R and R′ in CR or NR′ can be the same or different;
- wherein X is O, S, or Se;
- wherein the ligand LA is coordinated to an Ir atom;
- wherein the Ir atom is bonded to ring A through an Ir—C bond;
- wherein the Ir atom is also coordinated to at least one of:
- (1) a ligand LB and the compound has a structure Ir(LA)(LB)2, wherein LB has a structure
- wherein X1, X2, X3, X4, X5, X6, X7, and X8 are C, wherein Ra and Rb are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, or
- (2) a ligand LC and the compound has a formula of Ir(LA)2(LC), wherein LC has a structure
- wherein Ra, Rb, and Rc are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, and combinations thereof;
- wherein, when the Ir atom is coordinated to LB, Ring B is pyridine, Z1 is nitrogen, Z2 is carbon, and n=1;
- wherein each R, R′ and RB is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein any adjacent substituents are optionally joined or fused into a ring;
- wherein the ligand LA is optionally linked with ligand LB or ligand LC to comprise a tetradentate or hexadentate ligand.
22 more elements
A consumer product comprising an organic light-emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an organic layer, disposed between the anode and the cathode, comprising a compound having a ligand of Formula I:
- wherein ring B is a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein RB represents mono to the possible maximum number of substitution, or no substitution;
- wherein Z1 and Z2 are each independently selected from the group consisting of carbon or nitrogen;
- wherein A1, A2, A3, and A4 are each independently CR or N;
- wherein ring C is a 5 or 6-membered aromatic ring;
- n is 0 or 1;
- wherein when n is 0, A8 is not present, and A5, A6, and A7 are each independently selected from the group consisting of CR, NR′, O, S, and Se;
- wherein when n is 1, A1, A2, A3, A4, A5, A6, A7, and A8 are each independently CR, and the Rs of two adjacent A5, A6, A7, and A8 are joined together to form a six-membered ring fused to ring A or ring C;
- wherein each R and R′ in CR or NR′ can be the same or different;
- wherein X is O, S, or Se;
- wherein the ligand LA is coordinated to an Ir atom;
- wherein the Ir atom is bonded to ring A through an Ir—C bond;
- wherein the Ir atom is also coordinated to at least one of:
- (1) a ligand LB and the compound has a structure Ir(LA)(LB)2, wherein LB has a structure
- wherein X1, X2, X3, X4, X5, X6, X7, and X8 are C, wherein Ra and Rb are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, or
- (2) a ligand LC and the compound has a formula of Ir(LA)2(LC), wherein LC has a structure
- wherein Ra, Rb, and Rc are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, and combinations thereof;
- wherein, when the Ir atom is coordinated to LB, Ring B is pyridine, Z1 is nitrogen, Z2 is carbon, and n=1;
- wherein each R, R′ and RB is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein any adjacent substituents are optionally joined or fused into a ring;
- wherein the ligand LA is optionally linked with ligand LB or ligand LC to comprise a tetradentate or hexadentate ligand.
22 more elements
Dependencies are inferred from the claim text.